3-Ethyl-1-pentyn-3-ol → HCID 57443527、化合物

HRID 547071ノート

反応式

HRID 547071 の反応式
[CH2:1]([C:3]([OH:8])([CH2:6][CH3:7])[C:4]#[CH:5])[CH3:2].[CH3:9][O:10][C:11](=[O:45])[CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([CH2:43][CH3:44])([C:28]3[CH:33]=[CH:32][C:31](OS(C(F)(F)F)(=O)=O)=[C:30]([CH3:42])[CH:29]=3)[CH2:26][CH3:27])=[CH:21][CH:20]=2)[CH:18]=1.C(=O)(O)[O-].[Na+]>C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[Cu]I>[CH3:9][O:10][C:11](=[O:45])[CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([C:19]2[CH:20]=[CH:21][C:22]([C:25]([CH2:43][CH3:44])([C:28]3[CH:33]=[CH:32][C:31]([C:5]#[C:4][C:3]([CH2:6][CH3:7])([OH:8])[CH2:1][CH3:2])=[C:30]([CH3:42])[CH:29]=3)[CH2:26][CH3:27])=[CH:23][CH:24]=2)[CH:18]=1

参加物

7

反応物 3

HCID 226983-Ethyl-1-pentyn-3-olHCID 516892Sodium BicarbonateHCID 57709113(5-{4-[1-Ethyl-1-(3-methyl-4-trifluoromethanesulfonyloxy-phenyl)-propyl]-phenyl}-pyridin-3-yl)-acetic acid methyl ester

生成物 1

HCID 57443527HCID 57443527、化合物収率 78.3%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8471Triethylamine溶媒

反応条件

温度
160 °C

実験手順

3-Ethyl-1-pentyn-3-ol (0.024 mL, 0.188 mmol), a [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II), dichloromethane complex (1:1) (10.6 mg, 0.013 mmol) and copper (I) iodide (2.5 mg, 0.013 mmol) were added to a solution of (5-{4-[1-ethyl-1-(3-methyl-4-trifluoromethanesulfonyloxy-phenyl)-propyl]-phenyl}-pyridin-3-yl)-acetic acid methyl ester (Example 144-(2); 67 mg, 0.125 mmol) in triethylamine (2 mL), and the mixture was stirred with microwave heating at 160° C. for three minutes. The reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=1:1) to give the target compound (48.7 mg, 78%).

後処理

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-a10a42cca6f44efcb0c862343fb0636b
出典データセット
uspto-grants-2011_05
特許番号
US07935688B2

反応ノート

読み込み中…